tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate → HCID 86699857, compound

HRID 1423310Notes

Reaction equation

HRID 1423310 reaction equation
[C:1]([CH:3]1[C:7](=O)[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1)#[N:2].[C:16]1([C:22]2[N:27]=[CH:26][C:25]([C:28]3[CH:29]=[N:30][NH:31][C:32]=3[NH2:33])=[CH:24][CH:23]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1(C)C=CC=CC=1>[NH2:2][C:1]1[N:31]2[N:30]=[CH:29][C:28]([C:25]3[CH:26]=[N:27][C:22]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[CH:23][CH:24]=3)=[C:32]2[N:33]=[C:7]2[CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4][C:3]=12

Participants

4

Reactant 2

HCID 2756790tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylateHCID 66980248HCID 66980248, compound

Product 1

HCID 86699857HCID 86699857, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
115 °C

Procedure

A mixture of tert-butyl 3-cyano-4-oxopyrrolidine-1-carboxylate (60.3 mg, 0.28 mmoL) and 4-(6-phenylpyridin-3-yl)-1H-pyrazol-5-amine (67.8 mg, 0.28 mmoL) in toluene (5 mL) was heated at 115° C. overnight. Concentration afforded crude tert-butyl 8-amino-3-(6-phenylpyridin-3-yl)-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate, which was converted to 3-(6-phenylpyridin-3-yl)-6,7-dihydro-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidin-8-amine by the treatment of 20% TFA/CH2Cl2 at room temperature: LCMS tR=0.38 Min (5 min run, UV254nm), Mass calculated for, M+328.1, observed LC/MS m/z 329.2 (M+H).

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-306a8298f81047f39615758da47ac1fa
Source dataset
uspto-grants-2015_01
Patent number
US08927562B2

Reaction notes

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